Cationic Rhodium(I)-Catalyzed Regioselective Tandem Heterocyclization/[3+2] Cycloaddition of 2-(1-Alkynyl)-2-alken-1-ones with Alkynes

被引:49
作者
Gao, Hongyin [1 ]
Zhang, Junliang [1 ,2 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai Inst Organ Chem, Beijing 100864, Peoples R China
关键词
cyclization; domino reactions; Lewis acids; regioselectivity; rhodium; transition metals; CATALYZED 5+2 CYCLOADDITIONS; 2+2+2 CARBOCYCLIZATION REACTIONS; HIGHLY SUBSTITUTED FURANS; DIELS-ALDER REACTION; PHOTOPHYSICAL PROPERTIES; POLYSUBSTITUTED FURANS; METAL; VINYLCYCLOPROPANES; CONSTRUCTION; HETEROCYCLES;
D O I
10.1002/chem.201103924
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rh I in two minds: A Rh I-catalyzed tandem heterocyclization/[3+2] cycloaddition reaction was developed that provides rapid, efficient, and stereoselective access to highly substituted cyclopenta[c]furans from readily available 2-(1-alkynyl)-2-alken-1-ones and alkynes (see scheme). The cationic Rh I acts as both a Lewis acid and a conventional transition-metal catalyst, providing the first example of a Rh I species acting as a Lewis acid. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2777 / 2782
页数:6
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